Imidazole → 5-(tert-Butyldimethylsilyloxy)-1H-indole

HRID 20984

Reaction equation

HRID 20984 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].C(=O)([O-])O.[Na+]>CN(C=O)C>[Si:16]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 160545-HydroxyindoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 222508175-(tert-Butyldimethylsilyloxy)-1H-indoleYield 133.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Hydroxyindole (209 mg, 1.57 mmol) was dissolved in DMF (6 mL), and the solution was added with imidazole (132 mg, 1.93 mmol) and tert-butyldimethylsilyl chloride (333 mg, 2.21 mmol) at 0° C. followed by stirring at room temperature for 3.5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution at 0° C. and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 5-(tert-butyldimethylsilyloxy)indole (517 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1f3d8217c1964a0ebeb2119a90db494a
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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